Ammonia → HCID 18382576, compound

HRID 2297605Notes

Reaction equation

HRID 2297605 reaction equation
[N+:1]([O-:4])([O-])=[O:2].[K+].[CH3:6][C:7]1([CH3:17])[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[N:8]1.N>S(=O)(=O)(O)O>[CH3:6][C:7]1([CH3:17])[CH2:16][C:15]2[C:10](=[CH:11][C:12]([N+:1]([O-:4])=[O:2])=[CH:13][CH:14]=2)[CH:9]=[N:8]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 24434Potassium NitrateHCID 110409823,3-dimethyl-3,4-dihydroisoquinoline

Product 1

HCID 18382576HCID 18382576, compoundYield 89.8%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
60 °C

Procedure

To a stirred solution of potassium nitrate (2.53 g) in sulfuric acid (14 ml ) at 0° C. was added dropwise a solution of 3,4-dihydro-3,3-dimethyl isoquinoline (3.68 g; 23 mmol) [prepared according to the procedure of T. J. N. Watson, J. Org. Chem., 1998, 63, 406] in sulfuric acid (13.5 ml). The resultant solution was stirred at room temperature for 1.5 h and then heated to 60° C. for 4.5 h. The solution was then cooled to room temperature, and poured on to ice.; 0.880 ammonia was added until the solution was neutral, and the product was extracted into dichloromethane (×3). The combined organic phases were, dried over magnesium sulphate, and then evaporated in vacuo to afford the title compound (4.22 g). 1H NMR (CDCl3)δ: 1.27 (6H, s), 2.85 (2H, s), 7.34 (1H, d, J=8 Hz), 8.17 (1H, d, J=2Hz), 8.23 (1H, dd, J=8, 2Hz), 8.33 (1H, s).

Workup

  1. customprepared
  2. temperatureThe solution was then cooled to room temperature
  3. additionpoured on to ice
  4. extractionthe product was extracted into dichloromethane (×3)
  5. dry with materialdried over magnesium sulphate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-9b4f380042da4077b684897c4c6c7c44
Source dataset
uspto-grants-2002_12
Patent number
US06492378B1

Reaction notes

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